Efficient asymmetric synthesis of [7]helicene bisquinones

Chemical Communications

Volumn , Issue 5, 2005, Pages 611-613

  Carreño, M Carmen ^a   González López, Marcos ^a   Urbano, Antonio ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 TOLYLSULFINYL) 1,4 BENZOQUINONE; 3,6 DIVINYL 1,2,7,8 TETRAHYDROPHENANTHRENE DERIVATIVE; BENZOQUINONE DERIVATIVE; HELICENE BISQUINONE DERIVATIVE; PHENANTHRENE DERIVATIVE; QUINONE DERIVATIVE; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

AROMATIZATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; ELIMINATION REACTION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; ISOMERIZATION; OPTICAL ROTATION; OXIDATION; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 14544298293     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b413879a     Document Type: Article

References (26)

1. For recent reviews on helicenes, see: F. Vögtle, Fascinating Molecules in Organic Chemistry, Wiley and Sons, New York, 1992, p. 156; H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, p. 321.
2. For recent reviews on helicenes, see: F. Vögtle, Fascinating Molecules in Organic Chemistry, Wiley and Sons, New York, 1992, p. 156; H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, p. 321.
3. S. Grimme, J. Harren, A. Sobanski and F. Vögtle, Eur. J. Org. Chem., 1998, 1491; T. J. Katz, Angew. Chem., Int. Ed., 2000, 39, 1921.
4. S. Grimme, J. Harren, A. Sobanski and F. Vögtle, Eur. J. Org. Chem., 1998, 1491; T. J. Katz, Angew. Chem., Int. Ed., 2000, 39, 1921.
5. A. Urbano, Angew. Chem., Int. Ed., 2003, 42, 3986.
6. M. Flammang-Barbieux, J. Nasielski and R. H. Martin, Tetrahedron Lett., 1967, 743.
7. F. B. Mallory and C. W. Mallory, Organic Reactions, Wiley & Sons, New York, 1984, Vol. 30, p. 1; W. H. Laarhoven, Organic Photochemistry, Marcel Dekker, New York, 1989, p. 163.
8. F. B. Mallory and C. W. Mallory, Organic Reactions, Wiley & Sons, New York, 1984, Vol. 30, p. 1; W. H. Laarhoven, Organic Photochemistry, Marcel Dekker, New York, 1989, p. 163.
9. Recent work: S. Maiorana, A. Papagni, E. Licandro, R. Annunziata, P. Paravidino, D. Perdicchia, C. Giannini, M. Bencini, K. Clays and A. Persoons, Tetrahedron, 2003, 59, 6481; R. El Abed, B. B. Hassine, J.-P. Genêt, M. Gorsane and A. Marinetti, Eur. J. Org. Chem., 2004, 1517.
10. Recent work: S. Maiorana, A. Papagni, E. Licandro, R. Annunziata, P. Paravidino, D. Perdicchia, C. Giannini, M. Bencini, K. Clays and A. Persoons, Tetrahedron, 2003, 59, 6481; R. El Abed, B. B. Hassine, J.-P. Genêt, M. Gorsane and A. Marinetti, Eur. J. Org. Chem., 2004, 1517.
11. See reference 3 and the following: I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, D. Šaman and P. Fiedler, Collect. Czech. Chem. Commun., 2003, 68, 917; K. Paruch, L. Vyklický and T. J. Katz, Org. Synth., 2003, 80, 233 and references cited therein.
12. See reference 3 and the following: I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, D. Šaman and P. Fiedler, Collect. Czech. Chem. Commun., 2003, 68, 917; K. Paruch, L. Vyklický and T. J. Katz, Org. Synth., 2003, 80, 233 and references cited therein.
13. Recent example: R. Fasel, K.-H. Ernst and M. Parschau, Angew. Chem., Int. Ed., 2003, 42, 5178.
14. Recent work: K. Tanaka, H. Osuga, H. Suzuki, Y. Shogase and Y. Kitahara, J. Chem. Soc., Perkin Trans. 1, 1998, 935.
15. J. M. Fox, N. R. Goldberg and T. J. Katz, J. Org. Chem., 1998, 63, 7456; K. E. S. Phillips, T. J. Katz, S. Jockusch, A. J. Lovinger and N. J. Turro, J. Am. Chem. Soc., 2001, 123, 11899 and references cited therein.
16. J. M. Fox, N. R. Goldberg and T. J. Katz, J. Org. Chem., 1998, 63, 7456; K. E. S. Phillips, T. J. Katz, S. Jockusch, A. J. Lovinger and N. J. Turro, J. Am. Chem. Soc., 2001, 123, 11899 and references cited therein.
17. A. Sudhakar and T. J. Katz, J. Am. Chem. Soc., 1986, 108, 179; K. Tanaka, H. Osuga, Y. Shogase and H. Suzuki, Tetrahedron Lett., 1995, 36, 915; K. Tanaka, Y. Kitahara, H. Suzuki, H. Osuga and Y. Kawai, Tetrahedron Lett., 1996, 37, 5925; H. Osuga, H. Suzuki and K. Tanaka, Bull. Chem. Soc. Jpn., 1997, 70, 891.
18. A. Sudhakar and T. J. Katz, J. Am. Chem. Soc., 1986, 108, 179; K. Tanaka, H. Osuga, Y. Shogase and H. Suzuki, Tetrahedron Lett., 1995, 36, 915; K. Tanaka, Y. Kitahara, H. Suzuki, H. Osuga and Y. Kawai, Tetrahedron Lett., 1996, 37, 5925; H. Osuga, H. Suzuki and K. Tanaka, Bull. Chem. Soc. Jpn., 1997, 70, 891.
19. A. Sudhakar and T. J. Katz, J. Am. Chem. Soc., 1986, 108, 179; K. Tanaka, H. Osuga, Y. Shogase and H. Suzuki, Tetrahedron Lett., 1995, 36, 915; K. Tanaka, Y. Kitahara, H. Suzuki, H. Osuga and Y. Kawai, Tetrahedron Lett., 1996, 37, 5925; H. Osuga, H. Suzuki and K. Tanaka, Bull. Chem. Soc. Jpn., 1997, 70, 891.
20. A. Sudhakar and T. J. Katz, J. Am. Chem. Soc., 1986, 108, 179; K. Tanaka, H. Osuga, Y. Shogase and H. Suzuki, Tetrahedron Lett., 1995, 36, 915; K. Tanaka, Y. Kitahara, H. Suzuki, H. Osuga and Y. Kawai, Tetrahedron Lett., 1996, 37, 5925; H. Osuga, H. Suzuki and K. Tanaka, Bull. Chem. Soc. Jpn., 1997, 70, 891.
21. M. C. Carreño, S. García-Cerrada and A. Urbano, J. Am. Chem. Soc., 2001, 123, 7929; M. C. Carreño, S. García-Cerrada and A. Urbano, Chem Commun., 2002, 1412-1413; M. C. Carreño, S. García-Cerrada and A. Urbano, Chem. Eur. J., 2003, 9, 4118.
22. M. C. Carreño, S. García-Cerrada and A. Urbano, J. Am. Chem. Soc., 2001, 123, 7929; M. C. Carreño, S. García-Cerrada and A. Urbano, Chem Commun., 2002, 1412-1413; M. C. Carreño, S. García-Cerrada and A. Urbano, Chem. Eur. J., 2003, 9, 4118.
23. M. C. Carreño, S. García-Cerrada and A. Urbano, J. Am. Chem. Soc., 2001, 123, 7929; M. C. Carreño, S. García-Cerrada and A. Urbano, Chem Commun., 2002, 1412-1413; M. C. Carreño, S. García-Cerrada and A. Urbano, Chem. Eur. J., 2003, 9, 4118.
24. R. B. Turner, D. E. Nettleton and R. Ferebee, J. Am. Chem Soc., 1956, 78, 5923.
25. M. C. Carreño, J. L. García Ruano and A. Urbano, Synthesis, 1992, 651.
26. T. Thongpanchang, K. Paruch, T. J. Katz, A. L. Rheingold, K. Lam and L. Liable-Sands, J. Org. Chem., 2000, 65, 1850.